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Definitions

• This invention relates to organometallic compounds. More specifically, this invention relates to organometallic compounds containing at least one benzofluorenyl ligand. In another aspect, this invention relates to polymerization catalyst systems which contain organometallic benzofluorenyl compounds. In still another aspect, this invention relates to a method for polymerizing olefins using such organometallic benzofluorenyl compounds and to the polymers resulting from such polymerizations.
• cyclopentadienyl structure refers to the following structure.
• cyclopentadiene-type compounds refers to compounds containing the cyclopentadiene structure. Examples include unsubstituted cyclopentadiene, unsubstituted indene, unsubstituted fluorene, and substituted varieties of such compounds. Also included is tetrahydroindene. Thus polycyclic cyclopentadiene compounds are included within the term.
• cyclopentadiene-type metallocenes have been found useful in catalyst systems for the polymerization of olefins. It has been noted in the art that variations in the chemical structure of such cyclopentadienyltype metallocenes can have significant effects upon the suitability of the metallocene as a polymerization catalyst.
• An object of the present invention is to provide certain new benzofluorenyl-containing metallocenes. Another object of the present invention is to provide a method for preparing new benzofluorenyl-type metallocenes. Still another object of the present invention is to provide polymerization catalysts employing benzofluorenyl-type metallocenes. Still yet another object of the present invention is to provide processes for the polymerization of olefins using benzofluorenyl-type metallocene catalyst systems. Still yet another object of the present invention is to provide polymers produced using such benzofluorenyl-containing metallocene catalysts.
• new metallocenes of the formula R" x (FlR n )(CpR m )MeQ k wherein Fl is a fluorenyl radical; Cp is a cyclopentadienyl, indenyl, tetrahydro indenyl, or fluorenyl radical; each R is the same or different and is a halide or an organo radical having 1 to 20 carbon atoms; R" is a structural bridge linking (FlR n ) and (CpR m ); Me is metal selected from the group consisting of group IVB, VB, and VIB metals of the Periodic Table; each Q is the same or different and is selected from the group consisting of hydrocarbyl or hydrocarbyloxy radicals having 1 to 20 carbon atoms, hydrogen, and halogens, x is 1 or 0, k is a number sufficient to fill out the remaining valences of Me, n is a number in
• a method for forming benzofluorenyl-containing metallocenes comprising reacting an alkali metal salt of the selected henzofluorenyl compound with a transition metal compound of the formula MeQk in the presence of a non-halogenated solvent for the benzofluorenyl salt which solvent is non-coordinating with respect to the transition metal compound.
• a process for the polymerization of olefins comprising contacting said olefins under suitable reaction conditions with a catalyst system comprising a benzofluorenyl-containing metallocene as described above in combination with a suitable organoaluminum co-catalyst.
• novel metallocenes provided in accordance with the present invention fall into two broad general categories.
• One category involves metallocenes in which a benzofluorenyl radical, either substituted or unsubstituted, is bonded to another cyclopentadienyl-type radical by a bridging structure R" and both the benzofluorenyl and the cyclopentadienyl radicals of that bridged ligand are bonded to the metal.
• bridging structure R" both the benzofluorenyl and the cyclopentadienyl radicals of that bridged ligand are bonded to the metal.
• the other category deals with metallocenes which are unbridged, that is the benzofluorenyl-containing ligand, either substituted or unsubstituted, and the other cyclopentadienyl-type ligands that are bound to the metal are not bound to each other. These metallocenes are referred to as unbridged metallocenes.
• the metal Me is selected from the group IV, VB, or VIB metals of the Periodic Table.
• the currently preferred metals include titanium, zirconium, hafnium, chromium, and vanadium.
• R" can be selected from any suitable bridging structure. Typical examples include hydrocarbyl or heteroatom-containing alkylene radicals containing 1 to 20 carbon atoms, especially 2 to 20 carbon atoms; germanium; silicon; phosphorus; boron; aluminum; tin; oxygen; nitrogen; and the like.
• the bridge can even be a cyclic hydrocarbyl structure.
• R" bridge when hydrocarbyl,can be aromatic in nature, such as a phenyl-substituted alkylene.
• the currently most preferred bridges are hydrocarbyl or heteroatom-containing alkylene radicals having 1 to 20 carbon atoms.
• k is equal to the valence of Me minus 2.
• the substituents R can be selected from a wide range of substituents.
• the substituents R are each independently selected from halides or hydrocarbyl radicals having 1 to 20 carbon atoms.
• the hydrocarbyl radicals R are alkyl, aryl, or arylalkyl radicals. More preferably, the alkyl R radicals have 1 to 5 carbon atoms.
• n is at least 2 so that at least two adjacent positions on F1 are connected by four carbons so that there is at least one benzo substituent at the 1,2; 2,3; 3,4; 5,6; 6,7; or 7,8 position of F1.
• (FIRn) to have more than one benzo group and for the benzo group or the benzofluorenyl group to be substituted.
• the substituents on the benzo group can be the same as R, as defined above, but alkyl, aryl, and alkoxy substituents are particularly preferred.
• Each Q is a hydrocarbyl radical such as, for example, aryl, alkyl, alkenyl, alkaryl, or arylalkyl radical having from 1 to 20 carbon atoms, hydrocarbyloxy radicals having 1 to 20 carbon atoms, hydrogen, or halogen.
• exemplary Q hydrocarbyl radicals include methyl, ethyl, propyl, butyl, amyl, isoamyl, hexyl, isobutyl, heptyl, octyl, nonyl, decyl, cetyl, 2-ethylhexyl, phenyl, and the like.
• Exemplary halogen atoms include chlorine, bromine, fluorine, and iodine, and of these halogen atoms, chlorine is currently the most preferred.
• Exemplary hydrocarboxy radicals include methoxy, ethoxy, propoxy, butoxy, amyloxy, and the like.
• unbridged metallocenes falling within the scope of the above formula include bis(3,4-benzofluorenyl) zirconium dichloride, bis(l,2:7,8-dibenzofluorenyl) zirconium dimethyl, bis(2,3-benzofluorenyl) hafnium dichloride, bis(2,3:6,7-dibenzofluorenyl)zirconium dichloride, bis(2,5-dimethyl-7H-benzo (c) fluorenyl) zirconium dichloride, bis(6-isopropyl-llH-benzo (b) fluorenyl) zirconium dichloride, bis(2,3-henzofluorenyl)hafnium dichloride, (cyclopentadienyl)(3,4-benzofluorenyl) zirconium dichloride, (cyclopentadienyl) (2,3:6,7-di
• bridged metallocenes containing bridged benzofluorenyl ligands include for example 1-(cyclopentadienyl)-1-(3,4-benzofluorenyl)-1,1-(dimethyl)-methane zirconium dichloride, 1,2-di(3,4-benzofluorenyl) ethane zirconium dichloride, 1,3-di(3,4-benzofluorenyl) propane zirconium dichloride, 1,2-di(2,3:6,7- dibenzofluorenyl) ethane hafnium dichloride, 1,3-di(2,3-benzofluorenyl) propane hafnium dichloride, 1-(3,4-benzofluorenyl)-2-(methyl)-2-(fluorenyl) ethane zirconium dichloride, dimethylsilyl di(2,3:6,7-dibenzofluorenyl
• a particularly preferred type of metallocenes are bridged metallocenes containing at least one symmetrically substituted fluorenyl radical.
• symmetrically substituted refers to fluorenyl radicals having substituents on opposite portions of the Fluorenyl radical, such as for example 2,7-dialkylfluorenyl; 2,7-dicycloalkenylfluorenyl; 3,6-dialkylfluorenyl; 2,7-dihalo fluorenyl; 2,7-diarylfluorenyl; 1,8-dialkylfluorenyl; 4,5-dialkylfluorenyl; 2,7-diarylalkylfluorenyl; 2,3:6,7-dibenzofluorenyl; 3,4:5,6-dibenzofluorenyl; and the like.
• the currently preferred alkyl substituents have 1 to 20 carbon atoms, more preferably 1 to 6 carbon atoms, and most preferably 1 to 4 carbon atoms.
• the currently most preferred halide substituents are chloride, iodide, and bromide.
• Examples of aryl substituents include those having 6 to 20 carbon atoms, with those having 6 to 10 carbon atoms generally being more preferred.
• the arylalkyl substituents can contain 7 to 20 carbon atoms, more commonly 7 to 10 carbon atoms. It should be recognized that in certain instances if the bridge and the substituents on the (Fln) and/or (Cpm) are particularly bulky it may be difficult to prepare the ligand, the dialkali metal salt, or the metallocene.
• inventive metallocenes as well as related metallocenes can be prepared by reacting an alkali metal salt of the selected benzofluorenyl compounds with a suitable transition metal compound in a suitable solvent under suitable reaction conditions.
• the bridged benzofluorenyl ligands can be prepared using procedures of the type taught in U.S. Patent No. 5,191,132 and the aforementioned U.S. Patent application Serial No. 08/064,630 and 07/984,054. Some methylene-bridged benzofluorenyl ligands can be made by using 6-or 6,6-substituted fulvenes. Examples of fulvene reactions are disclosed in U.S. Patent No. 4,892,851 and in J. Organomet. Chem. 435, 299-310 (1992). In general,the technique involves reacting an alkali metal salt of the selected benzofluorene compound with the selected fulvene type compound.
• the 6,6-diphenyl fulvenes can be prepared by reacting a suitable aryl bromide, i.e. phenyl bromide, p-tolyl bromide, p-fluorophenyl bromide, or p-t-butylphenyl bromide, with magnesium to form a Grignard reagent, which is hydrolyzed. Then the dropwise addition of methyl formate results in the formation of the diarylcarbinol. The diarylcarbinol can then be oxidized smoothly to give the correspondingly substituted benzophenone, preferably using sulfuric acid and chromic acid. The resulting substituted benzophenone can then be reacted with cyclopentadiene in ethanol. containing sodium ethoxide to yield the 6,6-substituted fulvene.
• a suitable aryl bromide i.e. phenyl bromide, p-tolyl bromide, p-fluoroph
• indanyl fulvene (which can also be called indanylidene fulvene) by reacting 1-indanone with cyclopentadiene in the presence of ethanol and sodium ethoxide.
• the indanyl fulvene is particularly useful in that it can be reacted with the alkali metal. salt of a fluorene compound, i.e. a benzofluorene, to yield an indanyl bridged fluorenyl cyclopentadienyl compound.
• a fluorene compound i.e. a benzofluorene
• An example would be 1-(3,4 benzofluorenyl)-1-(cyclopentadienyl) indanylidene.
• benzofluorenyl compounds needed to make the ligands can be prepared using procedures generally known in the prior art. See for example U.S. Patent No 3,615,412. Some particularly desirable techniques for forming certain of the benzofluorenyl compounds will be described in further detail in what follows.
• transition metal compound as used herein includes compounds of the formula MeQ k wherein Me, Q, and k are as defined above.
• Some non-limiting examples include zirconium tetrachloride, hafnium tetrachloride, titanium tetrachloride, cyclopentadienyl zirconium trichloride, fluorenyl evelopentadienyl zirconium dichloride, 3-methylcyclopentadienyl zirconium trichloride, indenyl cyclopentadienyl zirconium dichloride, 4-methyl fluorenyl zirconium trichloride, pentamethylcyclopentadienyl zirconium trichloride, and the like.
• Inventive metallocenes in which Q is hydrocarbyl or hydrocarbyloxy can be readily prepared by reacting the halide form of the metallocene with an alkali metal salt of the hydrocarbyl or hydrocarbyloxy radical under conditions as have been used in the past for forming such ligands in prior art metallocenes. See, for example, the aforementioned J.Organomet. Chem. 113, 331-339 (1976). Another approach involves reacting a compound of the formula MeQ k wherein at least one Q is hydrocarbyl or hydrocarbyloxy, with the alkali metal salt of the bridged or unbridged benzofluorenyl compound.
• One embodiment of the present invention involves carrying out the reaction of the benzofluorenyl-containing salt and the transition metal compound in the presence of a liquid diluent which is non-halogenated and non-coordinating toward the transition metal compound.
• suitable liquid include hydrocarbons such as toluene, pentane, or hexane as well as non-cyclic ether compounds such as diethylether. It has been found that the use of such non-halogenated non-coordinating solvents generally allows one to obtain large amounts of substantially pure metallocenes and in a more stable form; and also often allows the reaction to be conducted under higher temperature conditions, than when dichloromethane is used as the diluent.
• the benzofluorenyl-containing salt used as a ligand is also prepared in a liquid diluent that is non-halogenated and non-coordinating toward the transition metal.
• the formation of the alkali metal salt of the bridged or unbridged benzofluorenyl compound can be formed using generally any technique known in the art.
• such can be prepared by reacting an alkali metal alkyl with the cyclopentadienyl type compounds or the bridged compounds having two cyclopentadienyl-type radicals per molecule.
• the molar ratio of the alkali metal alkyl to the cyclopentadienyl type radicals present can vary, generally however, the ratio would be in the range of about 0.5/1 to about 1.5/1, still more preferably about 1/1.
• the alkali metal of the alkali metal alkyl would be selected from sodium, potassium, and lithium, and the alkyl group would have 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms.
• the benzofluorenyl salt is formed using tetrahydrofuran (THF) as the liquid solvent, the salt is isolated, and substantially all of the THF is removed before the salt is contacted with the transition metal halide.
• the molar ratio of the bridged or unbridged benzofluorenyl alkali metal compound to the transition metal compound can vary over a wide range depending upon the results desired. Typically, however, when an unbridged benzofluorenyl alkali metal compound is used, the molar ratio of the unbridged benzofluorenyl compound to the transition metal compound is in the range of from about 1 to 1 to about 2 to 1. When a bridged benzofluorenyl alkali metal compound is used,the molar ratio of the bridged benzofluorenyl alkali metal compound to the transition metal compound is about 1 to 1 when one desires a bridged metallocene and about 2 to 1 when one desires an unbridged metallocene.
• the resulting metallocene can be recovered and purified using conventional techniques known in the art such as filtration, extraction, crystallization, and re-crystallization. It is generally desirable to recover the metallocene in a form that is free of any substantial amount of by-product impurities. Accordingly, recrystallization and fractional crystallization to obtain relatively pure metallocenes are desirable. Dichloromethane has been found to be particularly useful for such recrystallizations. As a general rule, it has been found that the metallocenes based on unbridged fluorenyl compounds are less stable than the metallocene compounds formed from bridged fluorenyl compounds.
• the metallocenes Since the stability of the various metallocenes varies, it is generally desirable to use the metallocenes soon after their preparation or at least to store the metallocene under conditions favoring their stability. For example,the metallocenes can generally be stored at low temperature, i.e. below 0°C in the absence of oxygen or water.
• the resulting benzofluorenyl-containing metallocenes can be used in combination with a suitable co-catalyst for the polymerization of olefins.
• a suitable co-catalyst for the polymerization of olefins.
• the metallocene or the co-catalyst can be employed on a solid insoluble particulate support.
• suitable co-catalysts include generally any of those organometallic co-catalysts which have in the past been employed in conjunction with transition metal-containing olefin polymerization catalysts.
• organometallic compounds of metals of Groups IA, IIA, and IIIB of the Periodic Table examples include organometallic halide compounds, organometallic hydrides and even metal hydrides.
• organometallic halide compounds organometallic hydrides and even metal hydrides.
• Some specific examples include triethyl aluminum, tri-isobutyl aluminum, diethyl aluminum chloride, diethyl aluminum hydride, and the like.
• Other examples of known cocatalysts include the use of a stable non-coordinating counteranion technique suc] as disclosed in U.S.
• Patent 5,155,080 e.g. using triphenyl carbenium tetrakis(pentafluorophenyl)boronate.
• Another example would be the use of a mixture of trimethylaluminum and dimethylfluoroaluminum such as disclosed by Zambelli et al., Macromolecules, 22 , 2186 (1989). In such processes the metallocene or the co-catalyst can be employed on a solid insoluble support.
• the currently most preferred co-catalyst is an aluminoxane.
• Such compounds include those oligomeric or polymeric compounds having repeating units of the formula where R is an alkyl group generally having 1 to 5 carbon atoms.
• Aluminoxanes also sometimes referred to as poly(hydrocarbyl aluminum oxides),are well known in the art and are generally prepared by reacting an organo aluminum compound with water. Such preparation techniques are disclosed in U.S. 3,242,099 and 4,808,56), the disclosures of which are incorporated herein by reference.
• the currently preferred co-catalysts are prepared either from trimethylaluminum or triethylaluminum, sometimes referred to as poly(methyl aluminum oxide) and poly(ethyl aluminum oxide), respectively. It is also within the scope of the invention to use an aluminoxane in combination with a trialkylaluminum, such as disclosed in U.S. Patent No. 4,794,096, the disclosure of which is incorporated herein by reference
• the fluorenyl-containing metallocenes in combination with the aluminoxane co-catalyst can be used to polymerize olefins. Generally such polymerizations would be carried out in a homogeneous system in which the catalyst and co-catalyst were soluble; however, it is within the scope of the present invention to carry out the polymerizations in the presence of supported forms of the catalyst and/or co-catalyst in a slurry or gas phase polymerization.
• the fluorenyl-containing metallocenes when used with aluminoxane are particularly useful for the polymerization of mono-unsaturated aliphatic alpha-olefins having 2 to 10 carbon atoms.
• olefins include ethylene, propylene, butene-1, pentene-1, 3-methylbutene-1, hexene-1, 4-methylpentene-1, 3-ethylbutene-1, heptene-1, octene-1, decene-1, 4,4-dimethyl-1-pentene, 4,4-diethyl-1-hexene, 3,4-dimethyl-1-hexene, and the like and mixtures thereof.
• the catalysts are particularly useful for preparing copolymers of ethylene or propylene and generally a minor amount, i.e. about 20 to 10 mole percent, more commonly about 12 mole percent, still more typically less than about 10 mole percent, of a higher molecular weight olefin.
• the polymerizations can be carried out under a wide range of conditions depending upon the particular metallocene employed, and the results desired.
• Examples of typical conditions under which the metallocenes can be used in the polymerization of olefins include conditions such as disclosed in U.S. Patents 3,242,099; 4,892,851; and 4,530,914; the disclosures of which are incorporated herein by reference. It is considered that generally any of the polymerization procedures used in the prior art with any transition metal-based catalyst systems can be employed with the present fluorenyl-containing metallocenes.
• the molar ratio of the aluminum in the aluminoxane to the transition metal in the metallocene would be in the range of about 0.1:1 to about 10 5 :1 and more preferably about 5:1 to about 10 4 :1.
• the polymerizations would be carried out in the presence of liquid diluents which do not have an adverse effect upon the catalyst system.
• liquid diluents include propane, butane, isobutane, pentane, hexane, heptane, octane, cyclohexane, methylcyclohexane, toluene, xylene, and the like.
• the polymerization temperature can vary over a wide range, temperatures typically would be in the range of about -60°C to about 280°C, more preferably in the range of about 20°C to about 160°C. Typically the pressure would be in the range of from about 1 to about 500 atmospheres or greater.
• the polymers produced with this invention have a wide range of uses that will be apparent to those skilled in the art from the physical properties of the respective polymer.
• a Gringard solution was prepared in a two liter two-necked flask from 13.6 g of magnesium powder, 1,000 ml of diethylether, and 123 g of distilled 1-bromo-2-methylnaphthalene, Then 0.5 g of Ni(TPP) 2 Cl 2 was added and 114 g of iodobenzene was added dropwise with stirring. The light brown suspension became hot and was heated for further 10 hours under reflux. The resulting reaction product was hydrolyzed and then extracted with ether, dried and freed from the solvent. By vacuum distillation, an orange liquid was obtained which was determined to be 2-methyl-1-phenylnaphthalene
• the suspension was poured into a large glass beaker containing 1000 ml of water to dissolve the magnesium dioxide by the portion-wise addition of dilute HCl and Na 2 SO 3 .
• the product 1-phenylnaphthalene-2-carboxylic acid was isolated by extraction with ether together with extraction of the organic phase with aqueous carbonate solution. This carboxylic acid product was then reacted with polyphosphoric acid. Specifically, 250 g of polyphosphoric acid were heated to 100-120°C in a 1000 ml flask. Then 23.9 g of the 1-phenylnaphthalene-2-carboxylic acid were added in portions, and the mixture allowed to stand for 1 hour at that temperature.
• the isomeric mixture of the 1,2-ethylene bridged-bis 3,4-benzofluorene ligand was dissolved in diethyl ether and stirred with two molar equivalents of n-butyllithium for at least 8 hours at room temperature.Then one molar equivalent of zirconium tetrachloride was added. The mixture was stirred for several more hours. The complex was extracted with dichloromethane and filtered over Na 2 SO 4 . A solid precipitates out at about -25°C to yield an approximately equal mixture of the rac- and meso-forms of the 1,2-bis-(3,4-benzofluorenyl) ethane zirconium dichloride.
• Ethylene homopolymerization was carried out using the metallocene of Example II.
• the polymerization was conducted in a 1-liter autoclave using 0.04 mg of the 1,2-di-(9-(3,4-benzofluorenyl)) ethane zirconium dichloride in 300 ml of hexane with 1 ml of a 30 wt% toluene solution of methylaluminoxane. After this, an ethylene pressure of 10 bar was applied and the reaction mixture stirred for 1 hour at 60°C. The recovered polymer was dried using a vacuum. A yield of 27.3 g of polymer was obtained. This translates to an activity of 4.2 x 10 5 g of polyethylene/mol zirconium-hour.
• a metallocene was prepared by dissolving 5 g of 3,4-benzofluorene in 100 ml of ether, and then a molar equivalent of n-butyllithium in hexane was slowly added. The liquid was then stirred for several hours at room temperature. Then a molar equivalent quantity of 6,6-dimethylfulvene was added and stirring was continued at room temperature. Decoloration of the solution occurred quickly. Then approximately 1 molar equivalent of n-butyllithium was added in order to transform any possible excess fulvene into a readily soluble colorless derivative. The mixture was then stirred for further 30 minutes end then hydrolyzed with a little water. The resulting dimethylmethylene-bridged ligand was then isolated and purified by dissolving in a solvent, filtering over silica gel and crystallization.
• 1-(3,4 benzofluorenyl)-1,1-diphenyl-l-(cyclopentadienyl) methane was prepared using a procedure similar to that used in Example IV but starting with 6,6-diphenylfulvene. In this preparation it was necessary to stir the reaction mixture overnight to obtain the desired degree of reaction.
• the dimethylmethane-bridged benzofluorenyl metallocene of Example TV was evaluated for the polymerization of propylene.
• Polymerization grade propylene was condensed into a 1-liter autoclave reactor. It was stirred for 15-30 min with 10 ml of a 30 wt% methylaluminoxane solution at 20°C and then cooled down to a temperature in the range of 0 to -2°C.
• a catalyst solution was prepared by combining the metallocene of Example IV with 1 ml of a 30 wt% solution of methylaluminoxane in toluene. The catalyst solution was forced into the cool stirred autoclave using argon pressure.
• the temperature was then brought to 60°C and maintained at that temperature for 120 min and then the polymerization was terminated by draining the unconsumed propylene.
• the polymerization demonstrated an activity of 34.9 x 10 3 kg of polypropylene per mol Zr-hr.
• the polymer had a nominal molecular weight of 37.5 x 10 3 g/mol. This was determined using a precision capillary viscometer in decalin at 135°C. For the determination, calibration curves were available for three different polymer concentrations. From 13 C-NMR it was determined that the polymer had a racemic content of 93.7, i.e., it would be viewed as a syndiotactic polymer.
• the resulting polypropylene had an isotacticity of 34.3%, a heterotacticity of 39.7%, and a syndiotacticity of 25.9% as determined by 13 C-NMR.
• the polymer had a melt flow of 204.
• the molecular weight as determined by size exclusion chromatography was 39,000.
• the nominal molecular weight was 5,000.

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